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Manipulación de la nucleofilidad del soluto con líquidos iónicos a temperatura ambiente.

Lorna Crowhurst1, N Llewellyn Lancaster, Juan M Pérez-Arlandis

  • 1Contribution from the Department of Chemistry, Imperial College London, South Kensington Campus, London SW7 2AZ, United Kingdom.

Journal of the American Chemical Society
|September 16, 2004
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Los líquidos iónicos mejoran la nucleofilicidad de las aminas, a diferencia de su efecto desactivador sobre los iones cloruro. Esta diferencia de reactividad se debe principalmente a entropias de activación alteradas y propiedades de enlace de hidrógeno del disolvente.

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Área de la Ciencia:

  • Química Física es la química física.
  • Química orgánica es la química orgánica.
  • Ciencia de los materiales Ciencia de los materiales.

Sus antecedentes:

  • Los líquidos iónicos (IL) son disolventes sintonizables con propiedades únicas.
  • Comprender el efecto de las IL en las reacciones nucleófilas es crucial para la química sintética.
  • El comportamiento de los nucleófilos de carga neutra en los IL es menos explorado que en los iónicos.

Objetivo del estudio:

  • Investigar el impacto de las ILs en la reactividad de los nucleófilos de aminas neutras en carga.
  • Para comparar la nucleofilicidad de las aminas en ILs versus disolventes moleculares.
  • Para aclarar los factores que rigen estos cambios de reactividad.

Principales métodos:

  • Se estudiaron las reacciones de (n) butilamina, di-n) butilamina y tri-n) butilamina con metil p-nitrobenzenosulfonato.
  • Se utilizaron tres líquidos iónicos: [bmpy][N(Tf)(2)], [bmpy][OTf], y [bmim][OTf].
  • Comparó las reactividades de las IL con las del diclorometano y el acetonitrilo; analizó los parámetros de activación de Eyring y los parámetros del disolvente de Kamlet-Taft.

Principales resultados:

  • Todas las aminas estudiadas mostraron una mayor nucleofilidad en líquidos iónicos en comparación con los disolventes moleculares.
  • Los líquidos iónicos desactivaron los nucleófilos de los iones cloruro, lo que contrasta con el comportamiento de las aminas.
  • Los cambios en la entropía de activación se identificaron como el principal impulsor de las tendencias de reactividad observadas.

Conclusiones:

  • Los líquidos iónicos modulan significativamente la reactividad de los nucleófilos de carga neutra.
  • Las interacciones de enlace de hidrógeno entre las IL y los nucleófilos juegan un papel clave en los efectos observados.
  • Los distintos efectos de las IL en los nucleófilos cargados frente a los neutros resaltan su complejo comportamiento de solvación.